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Jackson-Cohen was born in Westminster, London.[5] His mother, Betty Jackson, is an English fashion designer, and his father, David Cohen, who is French-Israeli, is his mother's business partner. Because of his French heritage he attended French school at the Lycée Français Charles de Gaulle in London[6] and claims to have a slight French accent.[7][8]

On leaving school, Oliver was advised to treat acting as a hobby rather than a career. After a role in a play at the Lyric Theatre got him an agent, he began attending auditions and put university on hold to apply for a place at drama school in New York. Shortly afterwards he received his first role.[9]

He also studied with Michael Luggio at the Malisa Theatre Academy.[10] He attended the Youngblood Theatre Company at weekends, and at 15 landed a small part in Hollyoaks. After school, he began a degree in French literature lasting "for about two weeks. I hated it." He soon got a job washing vases for a florist to keep him going between auditions. "It wasn't great but when you're that broke you'll do anything."[11]